Acetyl chloride → HCID 49805522, compound

HRID 577223Notes

Reaction equation

HRID 577223 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH3:18])[C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=1.[C:19](Cl)(=[O:21])[CH3:20].C(N(CC)CC)C>ClCCl>[C:19]([O:16][C:14]1[CH:13]=[C:12]([CH3:17])[N:11]=[C:10]([S:9][CH2:8][C:7]2[C:6]([CH3:18])=[CH:5][N:4]=[CH:3][C:2]=2[Cl:1])[N:15]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178429449HCID 178429449, compound

Product 1

HCID 49805522HCID 49805522, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round bottom flask, 2-{[(3-chloro-5-methylpyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (565 mg, 2.0 mmol) was dissolved in dichloromethane (25 mL). Acetyl chloride (0.21 mL, 3.0 mmol) was added, followed by triethylamine (0.42 mL, 3.0 mmol). After 30 minutes, the reaction mixture was evaporated. The crude product was purified by column chromatography (0˜35% ethyl acetate/hexane) to provide 2-{[(3-chloro-5-methylpyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-yl acetate as a white solid (500 mg, 77% yield); 1H NMR (500 MHz, CDCl3): δ 2.35 (s, 3H), 2.45 (s, 3H), 2.52 (s, 3H), 4.57 (s, 2H), 6.73 (s, 1H), 8.29 (s, 1H), 8.44 (s, 1H); M+ 324.

Workup

  1. customthe reaction mixture was evaporated
  2. customThe crude product was purified by column chromatography (0˜35% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c5f0399f535440069afdb60be0075d84
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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